(2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

Base Information

• Chemical Name: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester
• CAS No.: 1262015-07-5
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 1262015-07-5.mol

Synonyms:cis-N-Benzyloxycarbonyl-3-hydroxyprolin;(2S,3R)-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester;

Chemical Property of (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

Chemical Property:

• Boiling Point: 486.9±45.0 °C(Predicted)
• PKA: 3.67±0.40(Predicted)
• PSA: 87.07000
• Density: 1.416±0.06 g/cm3(Predicted)
• LogP: 0.78090

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester

There total 7 articles about (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C14H15NO5 (1290130-76-5) → (2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1262015-07-5)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In acetonitrile; at 15 ℃; for 12h;

DOI:10.1016/j.tetlet.2010.10.086

Reference yield:

3,6-epimino-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose (107690-61-9) → (2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1262015-07-5)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate / water; methanol / 3 h / 0 °C

2: trifluoroacetic acid / water

3: sodium periodate / water; acetone

4: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / water / 0.33 h / 0 - 20 °C

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; dihydrogen peroxide; sodium hydrogencarbonate; trifluoroacetic acid; In methanol; water; acetone;

DOI:10.1039/c5ra01340b

Reference yield:

(3aR,4aR,7aS,7bR)-2,2-dimethylhexahydro-6H-[1,3]dioxolo-[4,5]furo[3,2-b]pyrrol-6-one → (2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1262015-07-5)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C

2: sodium hydrogencarbonate / water; methanol / 3 h / 0 °C

3: trifluoroacetic acid / water

4: sodium periodate / water; acetone

5: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / water / 0.33 h / 0 - 20 °C

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dihydrogen peroxide; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1039/c5ra01340b

upstream raw materials:

C₁₄H₁₅NO₅

(1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane

3,6-epimino-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

Downstream raw materials:

(2S,3R)-3-hydroxyproline

cis-3-hydroxy-L-proline methyl ester

Refernces

• 1、 Kalamkar, Navnath B.,Kasture, Vijay M.,Dhavale, Dilip D.. "Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose". supporting information; experimental part. p. 6745 - 6747. Retrieved 2011/02/25.